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  • Versatile 8-oxabicyclo[3.2.1]oct-6-en-3-one: stereoselective methodology for generating C-glycosides, delta-valerolactones, and polyacetate segments.

Versatile 8-oxabicyclo[3.2.1]oct-6-en-3-one: stereoselective methodology for generating C-glycosides, delta-valerolactones, and polyacetate segments.

Organic letters (2001-06-30)
A Vakalopoulos, H M Hoffmann
ABSTRACT

[figure: see text] A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta-valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported. Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
γ-Valerolactone, ≥99%, FCC, FG
Sigma-Aldrich
γ-Valerolactone, ReagentPlus®, 99%
Sigma-Aldrich
γ-Valerolactone, natural, ≥95%, FG